Holy crap, KK, I'm SO HAPPY I'm not the first one to try and whale on an enemy...WITH A DOG.
Our poor ranger (who I got thrown into prison with me, and thus the arena) was killed by wargs, and had I managed to make it over to her in one less round, I could have administered healing. What stopped me? The worg I was fighting, who was being joined by the worg that critted the shit out of her. GM did a nice job of crunching numbers in a hurry and determined that if I was balls-out-lucky, I could land one of my flurry of blows hits on each of them and hopefully crit on them both.
My solution? "Fuck that. Grapple check on Fido here. I'm gonna' break his neck as I use him to bludgeon Pluto."
Sadly, Pluto proved a bit more resilient than we liked, and Miss Ranger died, but not before Pluto was hit with an unarmed strike crit that sent the arena spectators home with chunky souvenirs. The thought of the whole thing kind of makes me need a cigarette, for a multitude of reasons.
Anyways, I say all that to say this: way to improvise. You should look into the drunken master thing if Zak allows for prestige classes down the road.